Trifluoroacetic acid → 2-(4-Methoxyphenyl)-6-methoxy-1-tetralone

HRID 583125Notes

Reaction equation

HRID 583125 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)[C:10]([OH:12])=O)=[CH:5][CH:4]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:13][CH2:14][C:15]3[C:20](=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=3)[C:10]2=[O:12])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 215844042-(4-Methoxyphenyl)-4-(3-methoxyphenyl)butyric acid

Product 1

HCID 134065432-(4-Methoxyphenyl)-6-methoxy-1-tetralone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2.31 g(7.7 mmol) of 2-(4-methoxyphenyl)-4-(3-methoxyphenyl)butyric acid was dissolved in 30 mL of CH2Cl2 and cooled to 0° C. To this solution was added 3.4 mL (23.1 mmol) of trifluoroacetic acid, the reaction was allowed to proceed for 30 minutes. The reaction was quenched by pouring into an aqueous solution of NaHCO3. The organic layer was separated, washed twice with NaHCO3 solution washed twice with brine, dried with Na2SO4, and evaporated to a solid. This yielded 1.5 g of the title compound as a tan amorphous solid.

Workup

  1. customThe reaction was quenched
  2. additionby pouring into an aqueous solution of NaHCO3
  3. customThe organic layer was separated
  4. washwashed twice with NaHCO3 solution
  5. washwashed twice with brine
  6. dry with materialdried with Na2SO4
  7. customevaporated to a solid

Sources & evidence

ORD record
ord-298377251b1c40fababeec9789a45bcf
Source dataset
uspto-grants-1999_07
Patent number
US05929090

Reaction notes

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